I think it's important for all of us to weigh being- conservative analytically versus ready to act when the right deal presents itself.

Versus a built up tar/paper roof or vs. a rubber roof?  

The difference in going to school/classes when you have a clear picture or goal for why you're there, versus just doing it because you have to, is night and day.

Think one 100K home paid off versus 5 down payments on similar homes if they cash flow well.

Versus investing the cash into other avenues that yield a higher return. 

So, this is why I'm torn---emotional versus investment, old vs more expensive and new etc. $250,000 - I have options there. 

Also, I would likely put the type of property/street of the property location (versus an exact address), if this makes a difference.

Lucas you will get  a thousand answers on here.Most investors with large amounts of capital go into larger properties.The scale is easier and cheaper to manage around 4 to 5 % versus 10% on little houses ( if you have a bunch of houses in the same area you can get cheaper but it is doubtful to land that many at a price you like).What's likely more to happen is to buy in  a ton of different areas with a ton of PM companies to oversee as they will not usually cover the whole area. 

If I have to hire a pro, there is no portion stating that I need to keep receipts and prove it really, I just have to have the inspector come back to the house and verify that it is up to code.I guess I am just confused now as to what constitutes a do-it-myself kind of job versus what I have to hire someone to do.  

In essence, you'd end up paying likely 0% to 15% on your income versus the flat 30% withholding.